Hydrochloric Acid → 4-Ethoxycarbonylphenylboronic acid

Participants

Reaction Steps

A suspension of 4-(dihydroxyboryl)benzoic acid (5.0 g, 30.13 mmol) in ethanol (16.0 mL) was treated with 4N HCl in dioxane (34.0 mL), heated to reflux, stirred for 1.5 hours, and concentrated. The concentrate was partitioned between water (150.0 mL) and diethyl ether (100.0 mL) and the aqueous layer was extracted with diethyl ether (2×100 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated to provide the desired product. MS (APCI) m/e 194 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ8.07 (m, 2H), 7.81 (m, 2H), 4.41 (q, 2H), 1.41 (t, 3H).

Provenance & Evidence